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Holiday Rentals in Windsor

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Holiday Rentals in Windsor

The Dylin

4.0 star property
9.2 out of 10, Wonderful, (80)
"Nice, clean, well-equipped and well-decorated rooms. "
The Dylin

Charming 2-bed apartment with WiFi, AC in brilliant Madison

The price is €161
includes taxes & fees
21 Aug - 22 Aug
Charming 2-bed apartment with WiFi, AC in brilliant Madison

Two bedroom suite with city views in the heart of downtown Madison

9.8 out of 10, Exceptional, (33)
"Perfect for a weekend in Madison. A good location close to everything. "
The price is €390
includes taxes & fees
1 Sept - 2 Sept
Two bedroom suite with city views in the heart of downtown Madison

Quietwater Cottage-On Water/Nature/Birds/Canoe/Hike/Relaxing/ Hot Tub, Peaceful!

9.8 out of 10, Exceptional, (240)
"Cozy cabin, nestled in the outskirts of Baraboo. Great for the scenery and hiking. A chance to unplug and get away from the big city to spend quality time nature. "
Quietwater Cottage-On Water/Nature/Birds/Canoe/Hike/Relaxing/ Hot Tub, Peaceful!

One Bedroom King with Den with views of Lake Monona in the heart of downtown.

9.6 out of 10, Exceptional, (27)
"The property was beautiful, safe, and in a perfect location for the event we were attending!"
The price is €331
includes taxes & fees
1 Sept - 2 Sept
One Bedroom King with Den with views of Lake Monona in the heart of downtown.

Private Pool - HOT TUB - Sauna - Game Room - Pets

10.0 out of 10, Exceptional, (1)
"The Sun Prairie house perfectly met the goals for our family gathering of six adults and golden retriever for social and private space and so many entertainment options! The house was spotless, the neighborhood quiet, with Woodmans close by for shopping. We had 5 days of sunshine, golfing nearby courses, enjoying afternoon pool time, evening hot tub, and bug-free outdoor dining-so private and relaxing! We never ran out of room for food/drinks in the large volume fridge (loved the beverage...
Private Pool - HOT TUB - Sauna - Game Room - Pets

One Bedroom King with Den with views of the heart of downtown.

2.0 star property
10.0 out of 10, Exceptional, (23)
"Super clean, well lit, and beautiful view! Would definitely stay again."
The price is €319
includes taxes & fees
1 Sept - 2 Sept
One Bedroom King with Den with views of the heart of downtown.

Beautiful Cabin on Scenic WI River/Lake Wisconsin. Close to WI Dells and Madison

9.8 out of 10, Exceptional, (73)
"A top-notch experience. Beautiful views, completely stocked with everything you need to cook a breakfast or a dinner. Loved the whole week there. "
Beautiful Cabin on Scenic WI River/Lake Wisconsin. Close to WI Dells and Madison

COZY WATERFRONT CABIN, ON SUNSET BAY, LAKE WISCONSIN !! SUMMER AND WINTER FUN !!

10.0 out of 10, Exceptional, (87)
"Such a charming spot right on the lake! Direct access to the water, beautiful views, close to a bunch of fun bars and restaurants, and an easy drive to Devil’s Lake, Wisconsin Dells, and Madison. We stayed for a long weekend with our six month old, and it was great! Joe, the owner, is so friendly and responsive. Highly recommended!"
COZY WATERFRONT CABIN, ON SUNSET BAY, LAKE WISCONSIN !! SUMMER AND WINTER FUN !!

Amazing Lake Wisconsin Views!!! Newly Remodeled Cottage with Modern Amenities!

9.8 out of 10, Exceptional, (86)
"This was a great place to stay for a weekend getaway with some friends. Would love to come by again in the summer time "
Amazing Lake Wisconsin Views!!! Newly Remodeled Cottage with Modern Amenities!

Capital PrimeTime - 6 Miles from Madison w/ fireplace

10.0 out of 10, Exceptional, (24)
"Would recommend - very good location, nice space, and great host!"
The price is €568
includes taxes & fees
4 Aug - 5 Aug
Capital PrimeTime - 6 Miles from Madison w/ fireplace

Doty ★ Walk to Everything -Hotel Quality- Downtown

9.8 out of 10, Exceptional, (33)
"Had a great stay!"
Doty ★ Walk to Everything -Hotel Quality- Downtown

Studio queen with views of Lake Monona in the heart of downtown Madison

9.4 out of 10, Exceptional, (9)
"The property location is great, walking distance to great restaurants, the Farmers market, and close to walking/running trails. "
The price is €248
includes taxes & fees
1 Sept - 2 Sept
Studio queen with views of Lake Monona in the heart of downtown Madison

Lakeview Cabin > Unique Mid-Century Tucked in Bluff

10.0 out of 10, Exceptional, (15)
"Beautiful view and rolling hills made for a relaxing stay."
The price is €424
includes taxes & fees
25 Aug - 26 Aug
Lakeview Cabin > Unique Mid-Century Tucked in Bluff

ONE OF A KIND vacation rental with a view

10.0 out of 10, Exceptional, (139)
"This is our second stay and will gladly come back. It is easy to maneuver around Madison and the house is a spectacular vintage 80’s home. "
ONE OF A KIND vacation rental with a view

Conveniently Located just off University Avenue on Madison's West Side

10.0 out of 10, Exceptional, (124)
"Very spacious, well appointed house in a quiet neighborhood, convenient to Madison."
Conveniently Located just off University Avenue on Madison's West Side

Enjoy Nature with Full Comfort!

9.4 out of 10, Exceptional, (29)
"Great location, beautiful, clean, and friendly host"
The price is €116
includes taxes & fees
12 Aug - 13 Aug
Enjoy Nature with Full Comfort!

One Bedroom King with views of the heart of downtown.

2.0 star property
10.0 out of 10, Exceptional, (2)
"I loved the location and the area it was located. I really loved the view and the clearness of the place as well. It was very homey and cozy. "
The price is €296
includes taxes & fees
1 Sept - 2 Sept
One Bedroom King with views of the heart of downtown.

Two Bedroom with views of Lake Monona in the heart of downtown Madison

10.0 out of 10, Exceptional, (7)
"We loved everything about this property. Would definitely stay there again."
The price is €414
includes taxes & fees
1 Sept - 2 Sept
Two Bedroom with views of Lake Monona in the heart of downtown Madison

Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access

10.0 out of 10, Exceptional, (115)
"I was visiting from Chicago for a concert and was immediately sold with this property! I loved the hot tub and fireplace!! The whole house was clean and very bright! I will definitely stay again!"
Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Windsor Hotel Reviews

Frequently asked questions

Can I find a holiday rental in Windsor?

Yes, there are holiday rentals in Windsor close to Mousehouse Cheesehaus, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Windsor has a good selection of restaurants. Make sure you have time to check out the shopping and sporting events during your trip.

What are some of the best holiday rentals that Windsor has to offer?

Relax in this clean cozy 3 bedroom, 2 bath home in the heart of Madison. Perfect: This holiday home rental outside of Windsor is equipped with a BBQ, air conditioning and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a stovetop and a microwave.

What can I see and do in Windsor?

Explore the area and family-friendly sights such as Mousehouse Cheesehaus, or get out into nature at a spot like Olbrich Botanical Gardens. In the wider area, you’ll find East Towne Mall and Madison Area Technical College.

What are holiday rentals like in Windsor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windsor. Holiday rentals feature extras such as WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about cleanliness, holiday rentals can provide a sense of security away from shared hotel lifts and busy reception areas while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental a great option for a family getaway.